35475-03-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl-5-chlorothiophene-2-carboxylate is used as a synthetic intermediate for the development of various pharmaceuticals. Its unique structure allows it to be a key component in the creation of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl-5-chlorothiophene-2-carboxylate serves as an intermediate in the synthesis of compounds used in crop protection and pest management. Its role in developing effective and targeted agrochemicals is vital for enhancing agricultural productivity and sustainability.
Used in Organic Synthesis:
Methyl-5-chlorothiophene-2-carboxylate is utilized as a versatile building block in organic synthesis, enabling the creation of a wide range of organic compounds for various applications beyond pharmaceuticals and agrochemicals. Its reactivity and functional groups make it a valuable precursor in the synthesis of specialty chemicals and materials.

Upstream product

• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 74-88-4 methyl iodide 
• 70374-39-9 lornoxicam 
• 67-56-1 methanol 
• 3437-95-4 2-Iodothiophene 
• 56-23-5 tetrachloromethane 
• 1003-09-4 2-bromothiophene 
• 96-43-5 2-thienyl chloride 
• 7647-01-0 hydrogenchloride 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 
• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 6310-09-4 2-acetyl-5-chlorothiophene 

Downstream Products

• 1227664-24-5 5-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester 
• 1313610-83-1 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide thiocyanate 
• 1313610-84-2 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide phosphate 
• 1313610-85-3 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-hydroxy-2-naphthoate 
• 1047645-87-3 N-((1S)-2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-5-chloro-4-(4-fluoro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide trifluoroacetate 
• 1047645-88-4 N-((1S)-2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-5-chloro-4-(4-fluoro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride 
• 1047643-74-2 N-[(1S)-2-amino-1-(phenylmethyl)ethyl]-5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide 
• 1047630-55-6 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid 
• 351983-31-8 5-chloro-2-thiophenecarboxylic acid hydrazide 

Relevant academic research and scientific papers

Discovery of 3-(thiophen/thiazole-2-ylthio)pyridine derivatives as multitarget anticancer agents

A series of novel 3-(thiophen/thiazole-2-ylthio)pyridine derivatives were designed and synthesized as IGF-1R tyrosine kinase inhibitors. All the target compounds were tested for their IGF-1R kinase inhibitory activities and cytotoxicities against five cancer cell lines (K562, Hep-G2, HCT-116, WSU-DLCL2, and A549). Although all these compounds exhibited moderate to potent cancer cell proliferation inhibitory activities (the most potent compound 43 showed IC50 value of 1.3 ± 0.9 μM against WSU-DLCL2 cell line), IGF-1R inhibition were not observed. In order to identify the exact target of these analogues, selected compounds were further screened for various kinases. The results indicated that this series of compounds may exert their anticancer activities through inhibiting various kinases including FGFR 3, EGFR, JAK, and RON. In addition, cell cycle analysis of compound 43 on Hep-G2 cells showed cell cycle arrest at G1/G0 phase. All the experiments validated the potential of 3-(thiophen/thiazole-2-ylthio)pyridine analogues as multi-target anticancer agents.

Photochemical and DNA degradation studies on tenoxicam, lornoxicam, and their photolysis products

Tenoxicam and lornoxicam are nonsteroidal anti-inflammatory drugs, were subjected to photoirradiation at 254?nm led to the photodegradation of the pharmaceutical agents. Both, the isolated photodegradation products and the pharmaceutical agents were exami

Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives

CO2utilization is an attractive aspect as it allows the direct conversion of CO2into valuable chemicals. In this regard, direct incorporation of CO2into the C-H bond of heteroaromatic compounds is important due to the ubiquitous structural motifs of the heteroaromatic carboxylic acids. Herein, we report the Ag-catalyzed C-H carboxylation of thiophene derivatives. This new catalytic system involving a phosphine ligand and lithiumtert-butoxide enables the direct carboxylation of thiophenes under mild reaction conditions. Experimental studies revealed that the use oftert-butyl alkoxide is critical for the exergonic formation of an arylsilver intermediate, and the results were further supported by density functional theory calculations.

BUMETANIDE DERIVATIVES FOR THE THERAPY OF HYPERHIDROSIS

The present invention relates to bumetanide derivatives of formula (I) as well as pharmaceutical compositions comprising these compounds for use in the treatment or prevention of diseases/disorders involving Na+- K+- 2CI- - cotransporters (NKCCs), and particularly for use in the treatment or prevention of hyperhidrosis.

Synthesis and anti-endoplasmic reticulum stress activity of N-substituted-2-arylcarbonylhydrazinecarbothioamides

Misfolded or unfolded proteins are accumulated in lumen of endoplasmic reticulum (ER) in ER stress condition. It has been implicated in many pathological conditions such as Alzheimer’s disease, diabetic retinopathy, atherosclerosis, β-cell apoptosis and lung inflammation. We found a series of N-substituted-2-arylcarbonylhydrazinecarbothioamides to potently decrease ER stress signal, showing up to almost 300-fold better activity than 1-hydroxynaphthoic acid and tauro-ursodesoxycholic acid, positive controls, respectively. Structure?activity relationship (SAR) study showed that 2-arylcarbonyl moiety is critical for the activity of the hydrazinecarbothioamide analogues and side chains tethering on thioamide moiety were relatively insensitive to the activity. Some analogues were found to consistently exert the potency under more physiologically relevant condition where ER stress was induced by palmitic acid. ER stress markers such as CHOP and phosphorylated eIF2α and PERK were accordingly decreased in western blotting upon treatment of compound 4h. Potential ER stress inhibitory activity and novel structures could provide a novel platform for new chemical chaperone and therapy for protein misfolding diseases.

Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

Biaryl pyridine deubiquitinating enzyme inhibitor as well as preparation method and application thereof

The invention designs and synthesizes a biaryl pyridine deubiquitinating enzyme inhibitor. The biaryl pyridine deubiquitinating enzyme inhibitor has the structure which is shown as a general formula (I). The biaryl pyridine deubiquitinating enzyme inhibit

A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids

Herein, we present a study on the oxidation of aldehydes to carboxylic acids using three recombinant aldehyde dehydrogenases (ALDHs). The ALDHs were used in purified form with a nicotinamide oxidase (NOx), which recycles the catalytic NAD+ at the expense of dioxygen (air at atmospheric pressure). The reaction was studied also with lyophilised whole cell as well as resting cell biocatalysts for more convenient practical application. The optimised biocatalytic oxidation runs in phosphate buffer at pH 8.5 and at 40 °C. From a set of sixty-one aliphatic, aryl-Aliphatic, benzylic, hetero-Aromatic and bicyclic aldehydes, fifty were converted with elevated yield (up to >99%). The exceptions were a few ortho-substituted benzaldehydes, bicyclic heteroaromatic aldehydes and 2-phenylpropanal. In all cases, the expected carboxylic acid was shown to be the only product (>99% chemoselectivity). Other oxidisable functionalities within the same molecule (e.g. hydroxyl, alkene, and heteroaromatic nitrogen or sulphur atoms) remained untouched. The reaction was scaled for the oxidation of 5-(hydroxymethyl)furfural (2 g), a bio-based starting material, to afford 5-(hydroxymethyl)furoic acid in 61% isolated yield. The new biocatalytic method avoids the use of toxic or unsafe oxidants, strong acids or bases, or undesired solvents. It shows applicability across a wide range of substrates, and retains perfect chemoselectivity. Alternative oxidisable groups were not converted, and other classical side-reactions (e.g. halogenation of unsaturated functionalities, Dakin-Type oxidation) did not occur. In comparison to other established enzymatic methods such as the use of oxidases (where the concomitant oxidation of alcohols and aldehydes is common), ALDHs offer greatly improved selectivity.

Visible-Light-Mediated Radical Arylation of Anilines with Acceptor-Substituted (Hetero)aryl Halides

A visible-light-mediated, catalyst-free, direct (hetero)arylation of anilines with mild reaction conditions has been developed. The formation of a donor-acceptor complex between electron-withdrawing substituted (hetero)aryl halides and anilines allows, under blue LED irradiation, the synthesis of ortho and para (hetero)arylated anilines in moderate to good yields. The reaction has a high functional group tolerance. Spectroscopic studies confirmed the donor-acceptor complex formation between aniline and aryl halide.

Pyrazolo[1,5a]pyrimidines as a new class of FUSE binding protein 1 (FUBP1) inhibitors

The transcriptional regulator FUSE binding protein 1 (FUBP1) is aberrantly upregulated in various malignancies, fulfilling its oncogenic role by the deregulation of critical genes involved in cell cycle control and apoptosis regulation. Thus, the pharmaceutical inhibition of this protein would represent an encouraging novel targeted chemotherapy. Here, we demonstrate the identification and initial optimization of a pyrazolo[1,5a]pyrimidine-based FUBP1 inhibitor derived from medium throughput screening, which interferes with the binding of FUBP1 to its single stranded target DNA FUSE. We were able to generate a new class of FUBP1 interfering molecules with in vitro and biological activity. In biophysical assays, we could show that our best inhibitor, compound 6, potently inhibits the binding of FUBP1 to the FUSE sequence with an IC50value of 11.0 μM. Furthermore, hepatocellular carcinoma cells exhibited sensitivity towards the treatment with compound 6, resulting in reduced cell expansion and induction of cell death. Finally, we provide insights into the corresponding SAR landscape, leading to a prospective enhancement in potency and cellular efficacy.